How to Throw a Legendary Holiday Party Without Pissing Off Your Investors

Holiday season is here, and that means your startup needs to have a holiday party! I was just hanging with some Midwestern, non-techie friends of mine who work in “normal” jobs, and they were all going on about how they all skip their office holiday parties. They’re the cool kids after all, and, as they say “I spend enough time with those people at work. I don’t want to spend my personal life with them.”

But startups are crazy backwards land, and you basically live and breathe and poop and shower with your coworkers. So you’re going to holiday party with them too. This isn’t a recommendation from me, it’s a practical fact. I mean, really. You probably go out drinking with your coworkers two to three days a week already, at minimum. So it seems safe to say you’re going to have a holiday party with them, even if it’s just the five of you drunkenly realizing at 2 a.m. that oh hey, this could be your holiday party and woooooooo!

It’s actually kind of an interesting logic puzzle. If you and your startup cohorts go out practically every night together already, what makes a holiday party different than any other night of the year? Santa hats play a part. But really, the question should be turned on its head: “If we’re going to have a holiday party, what do we do to make it special?”

And so I am here to help you. I have thrown a fair number of holiday parties in my day. Some have reached the status of legend. Some failed miserably. The have ran from 10 to 1,000 people. Here’s what I’ve found that works.

I am speaking to lean startups here. If you’ve gotten your Series A and are viewing your holiday parties as PR opportunities, well, I feel sorry for you, and these rules do not apply. My strong recommendation to you is to not view your holiday party as a PR opportunity and follow these guidelines nonetheless.

First, if you’re going for that giant, most-important-party-of-the-season blowout, give up. I say this for three reasons. First, it’s already mid-December. It’s too late. To plan the ultimate blow up, you need to start planning that shit in June, July latest. Secondly, you’re a startup, and that has unfortunately been ruined for us all thanks to Razorfish back in the day with their “worst party ever” some 14 years ago.

Rumor has it they spent something like $15,000 on the party, which really isn’t that much compared to blowouts of recent years: I recently went to one for a major tech company where it was said they spent $150,000 on the band alone. Fact is, your startup can’t throw the most over-the-top party possible. Which leads me to my next point, nor should it. You’re a startup. You’re about thrift. It is unbecoming to blow too much of other people’s money on a party. You can pull this whole thing off in an awesome way for like, five grand, if you plan right. You can get by and still have it be pretty rad for like, two grand.

Next, clients. If you have clients, I strongly recommend you do not invite them. Or at least most of them. If you have a cool client, you can invite that person. Clients keep everyone on edge and inhibit the camaraderie and bonding experience of the party. If you need to do something for your clients for the holiday season, send them a gift or card. (Note: if you’re making cards, it takes a long time to think up something good. Start that project in, like, July as well.) Plus, they can’t handle their liquor. I don’t know what it is. They either stand in horror looking at the whole scene, or dive right in and lose their minds. I’ve had clients bleed on employees. I’ve caught them doing blow and unspeakable acts in dark corners. Just leave them at home.

The space is key. You are going for the most space possible for the least amount of money. If your office is big enough, do it there. If you do that, hire security, lock away your computers, hire caterers and hire a cleaning company. Trust me on this. People will puke, and even in an office of all people you know, something will get stolen. It’s a depressing insight into the human condition. Lock everything up, hire security, keep anything from getting stolen and live in ignorant bliss that one of your friends is a klepto. Caterers are vital because otherwise people are pouring keg beer into gallon jugs and lining their pockets with bottles. I remember walking out of our holiday party with my best friend, and there was the homeless man on the street that lived by our office. He asked for some change, and my friend pulled a full bar bottle of Grey Goose out of his coat, looked at me sheepishly and handed it to the homeless man. Holiday cheer.

If your office isn’t practical, since you work out of your home or a coworking space or something, go for the biggest, cheapest place you can find. This might mean a bar that is usually empty on a Tuesday night (you should rule out weekends for your holiday party—too expensive and people leave town). There are plenty of bars that will rope off an area if 20 people are coming. Have it at a dive bar. It will be cheaper for you, reinforce your sense of thrift to any guests who might care, and is generally more fun anyway. Plus it makes it clear you’re not trying to keep up with the Joneses. It shows that what you’re really doing is spending money on the most important thing: the booze.

When it comes to the booze, quantity is the order of the day here. Try and have an “open bar” in any way you can swing it. An open bar does wonders to a crowd’s psychology. It’s Bataille’s theory of potlatch. People have some latent psychological trigger in their head when excess doesn’t have to be reigned in and gloriously weird things happen. It’s the startup equivalent to Vegas buffets. If you’re on a budget, there are ways to limit the open bar but keep this sense of the unlimited. Tell the bar to keep the top shelf stuff off limits. Keep the duration of the open bar short (though I wouldn’t recommend against going under three hours). In a pinch, you can limit to beer and wine, but it’s really not as fun and the results aren’t as satisfactory. Better to have the whole thing at a cheaper bar, or get a sponsor for one hard booze.

Speaking of sponsors, I recommend against them. If you desperately need the free booze, or if you are working with a booze company that really wants to sponsor your party, then okay. But otherwise, try and avoid them. It interjects an ineffable sense of commerce into what should be a pure bonding experience.

Guest list: it’s totally okay to invite people beyond the employees. I generally invite beloved friends, vendors, contractors, etc. Though it might be a little awkward, I strongly encourage you to invite your investors (I am looking at you, my portfolio companies). If you’ve followed all of these steps, your party will be pretty manifestly thrifty so they shouldn’t be too agog at the waste. If you go this route, consider an hour or two at the beginning where it is just employees, so there’s a little bonding time. If you want to go employees-only I think that is totally okay too—especially if it allows the open bar to be open longer. I don’t personally like the employees+spouse route, and with startups and young people it can be slightly uncomfortable as many of them are just casually dating. Plus the older or more reserved employees then have a spouse to hide behind rather than getting tanked, which is no fun.

Finally, paying for the thing: this is what you do. Get a budget from your CFO. Then tell whoever is planning the party that budget. Make sure your CFO is getting nicely sloshed at the party. Have your company card handy. When the party is running near the budget, pull out the company card, give a wink to your CFO and say “let’s keep going! It’s on me!” Everyone will cheer. Sort it out with the CFO in a month with then bill comes in.

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